Since our currency so cheap to yours and you wouldn't be saddled with VAT, I assume a watch here in the US is cheaper than even a used one for you at home, no? Take a look at the bigger shops like Wempe and Tourneau and check US pricing.

I'm not a huge Rolex or Breitling fan, but why should you care about that? Buy what you like. Subs are nice, especially on a Nato strap and do hold their value quite well, so it's hard to go wrong with that.

Take a walk down 47th street (the diamond district) hundreds of pre owned dealers selling every type of watch. I have always window shopped, so I don't know what type of deals they offer on pre owned, or how much they will negotiate. I'm not a fan of the big T.

I think Rolex is one of the better values, a Sub will likely appreciate in value over time, and almost any competent watch maker can service a Rolex.